| 2. Ronde | 07.09.2008 | AS Cittadella | - | US Salernitana 1919 | 0:0 | ||||
| 3. Ronde | 13.09.2008 | US Avellino | - | AS Cittadella | 0:0 | ||||
| 5. Ronde | 23.09.2008 | Treviso FBC | - | AS Cittadella | 0:1 |  |
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| 6. Ronde | 27.09.2008 | AS Cittadella | - | Empoli FC | 0:2 | ||||
| 7. Ronde | 04.10.2008 | AS Cittadella | - | Vicenza Calcio | 0:1 | ||||
| 8. Ronde | 12.10.2008 | US Triestina | - | AS Cittadella | 2:1 | |
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| 9. Ronde | 18.10.2008 | AS Cittadella | - | AS Livorno | 0:0 | ||||
| 11. Ronde | 28.10.2008 | AS Cittadella | - | AS Bari | 1:1 | ||||
| 12. Ronde | 01.11.2008 | Modena FC | - | AS Cittadella | 3:3 |  |
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| 13. Ronde | 08.11.2008 | Sassuolo Calcio | - | AS Cittadella | 3:1 | ||||
| 14. Ronde | 15.11.2008 | AS Cittadella | - | UC AlbinoLeffe | 0:0 | ||||
| 15. Ronde | 22.11.2008 | Pisa Calcio | - | AS Cittadella | 0:3 | ||||
| 17. Ronde | 06.12.2008 | US Grosseto FC | - | AS Cittadella | 1:1 | ||||
| 18. Ronde | 13.12.2008 | AS Cittadella | - | Brescia Calcio | 2:0 |
Italië